Fashion essentials in a business setting

This is gonna be ultra embarrassing for a grown man in his 40s to ask, but I need some fashion advice from the men (and ladies!) on OUF…

My story is that I’ve been working as a freelancer for the past decade. It was a great way to make a living because I get to work from home and just wear whatever’s comfortable. On the days I don’t need to get out of the house, I don’t even need to change from my PJs. Since I don’t need to go anywhere important or fancy, my wardrobe consists of mostly t-shirts and jeans. As you can tell, I’m a hopeless schmuck with no fashion sense.

Unfortunately, it’s all about to change because I just got my first office job. After years of freelancing, I finally landed an actual full-time job that meets all my requirements. The good part is I still get to work from home on most days, but the bad part is I do have to show up to the office for meetings and presentations. This part is where I feel anxious, because I don’t know how to dress myself for the office. I’m at a complete loss.

I feel very humbled and I’m looking for some fashion advice. Thank you!

Hey, don’t feel embarrassed. We’ve all been there at some point in our lives. Starting your first day of work at your first job can be stressful and overwhelming. It’s understandable that you want to look your best and make first good impressions with your coworkers.

Most office environments should have a relaxed dress code. You shouldn’t have to get too dressed up for the office, but of course there are different dress codes for different workplaces. Did you go to the office for the interviews? Did you notice what the other people in the office were wearing? Just copy their style so you’ll blend right in.

I do have a suit that I wore for the interviews, but is that too formal to wear for the office? Most of my colleagues there were wearing business casual, so they do dress up and I’ll be standing out like a sore thumb if I show up in my t-shirt and jeans. Or would that be OK to wear?

It’s kinda embarrassing that I’m feeling so flustered over my wardrobe choices for work, but it’s such a new experience for me that I don’t know what to do. I don’t mind spending money on a new business wardrobe, but I wouldn’t even know what to buy. Last week I stepped into an actual store and felt so overwhelmed by all the choices (and price tags) that I stepped out empty-handed.

There’s no right answer here. What you wear to work also depends on what sector you work in. Some industries are more image-focused than others, so what is considered overdressed in one workplace setting might appear undressed in another work environment.

For my workplace, I wear business casual. Personally, I shop at Harry Rosen for the clothes, ALDO for the shoes, and Betty Hemmings for the accessories. All good reliable brands with a reasonable price range.

I want to emphasize the importance of fashion accessories. A pen, a watch, a briefcase – these simple items can enrich your overall outfit. For example, carrying a briefcase is a huge confidence builder from my experience. Just think: you walk into an office, you’re carrying a nice looking leather briefcase in your hand, you have some important documents inside. It will change your mindset. You’ll feel confident, you’ll feel important, and you’ll feel more relaxed knowing that you’re dressed to impress.

I’m going to leave the actual fashion recommendations to our male forum members, but my one piece of advice is please don’t show up to your first day of work in your t-shirt and jeans. You’re going to look like a sloppy college intern in your 40s. Maybe acceptable in the future after you relaxed into the role, but it just isn’t the right choice when you’re meeting everyone around the office. You don’t need to wear a suit, but you do need to put a little more effort into what you wear.

Now I feel very self-conscious because I showed up to my first office job in t-shirt and jeans. I didn’t think it was that big of a deal. Nobody commented on my outfit. Did they think I looked like a sloppy college intern too? 😛

For your first day of work, it’s better to be overdressed than underdressed. Nobody is going to judge you if you dressed up in a full blazer and suit, but there could be some raised eyebrows if you wear a t-shirt, shorts, and sandals. I’m not saying all workplaces are that strict, but given your description, I think I would err on the side of caution and simply wear a suit.

You have other things to worry about on your first day than feel self-conscious about how you look. If you wear a suit, you’re going to feel more confident and self-assured. Even if you’re severely overdressed, you can just laugh it off and this could be a nice icebreaker with your new colleagues.

Here’s a really good blog post about to what to wear on your first day of work.

How old is everyone in your office? I wouldn’t rule out jeans if your colleagues are on the younger side. I find that they tend to be less uptight about what to wear.

If you don’t want to get too dressed up, I think a dress shirt + a pair of black jeans might be a good combo. It’s a little casual, but it’s also ‘dressy’ enough for a professional environment. The outfit is a safe bet, and I don’t think people are going to judge you too much either way.

I hate to be THAT person, but are you guys possibly overthinking this? You aren’t there to put on a fashion show. Just wear whatever’s comfortable for you. At the end of the day, people are going to remember you for your work performance, not your appearance.

It’s not a guy thing, it’s just a practical thing. If Wallace showed up to my workplace in his t-shirt and shorts, I wouldn’t bat an eye. In fact, I’ll give him a pat on the back for his sensible fashion choices.

How is it sensible to wear shorts in an office environment when everyone else is dressed up in business attire!? Ryan, if you think that’s acceptable, I shudder to think what you actually wear in your office.